David Sole leads his Scotland team on to the field before the 1990 Five Nations Championship match at Murrayfield. Photograph: Russell Cheyne/Allsport

1) Scotland 1–0 England (1871)

It's "about three o'clock" on Saturday 5 March 1870, and at the Kennington Oval, south London, 22 "expert players" of the Association Football code set the ball in motion for a kickabout. But it's no ordinary game: it's the first-ever England versus Scotland international!

Except it's not, not really. Scotland's team isn't a Scottish team at all. Cobbled together by a shower down south, the "Scotland" XI's star man is Mr WH Gladstone, Welsh son of the serving prime minister. Most of the rest of the side are Londoners born within the sahnd of yer actual Bow Bells. The game ends in a 1-1 draw, England scrambling an equaliser in the dying seconds, though the Scots aren't having any of it. The game won't count. Everyone will have to wait until November 1872 for the first official football international. (And what a game that will be, 0-0 between Scotland and England at the West of Scotland Cricket Club, Partick. But that's a tale for another day.)

The impudence of the English in setting up the 1870 stramash without actually asking anyone north of the border about it! This sorry state of affairs led a collection of Scottish clubs – Edinburgh Academical, Glasgow Academical, West of Scotland, Merchistonian, and St Salvator of St Andrews – to challenge England's Football Association to an official international game of football. However, these clubs had – unlike the English, and a small smattering of folk in Scotland – yet to embrace association, and so the "football" challenge actually referred to the old rugby football rules.

Unsurprisingly, the FA – concentrating on new-fangled soccer – ignored this challenge, but Blackheath picked up the gauntlet and set about arranging a squad to represent England in a rugby game to be held at Raeburn Place, Edinburgh, on Monday 27 March 1871.

And so to the game which, sad to say, was a lot of nonsense. With both teams fielding 20 men, the match was effectively a 100-minute maul. It didn't help that the English considered the pitch far too narrow; it restricted their speedy backs, and played into the hands of a fitter and stronger Scottish pack.

After a scoreless first half, the Scots heaved Angus Buchanan over the line for rugby's first-ever international try. Whether it was kosher or not is a moot point: it was unclear whether the ball had been grounded, and referee Dr HH Almond – a local headmaster instrumental in the early development of rugby in Scotland – had a decision to make. With England complaining vociferously, he sided with the Scots, arguing that "when an umpire is in doubt, he is justified in deciding against the side which makes the most noise. They are probably in the wrong." And yet Buchanan's try didn't trouble the scorers; all it did was give place kicker William Cross the chance to "try" for a goal. Cross converted the kick for one rugby football point!

England crossed the tryline themselves through Reginald Birkett – who would later play for the soccer team in between the sticks – but his try wasn't converted. Cross went over for Scotland – umpire Almond again at the centre of controversy, this time ignoring a knock-on – but he missed his second kick, and the game ended 1-0 to the Scots.

2) England 16–21 Scotland (1938)

One hundred years later to the day, Murrayfield staged a friendly to commemorate the centenary of that historic game. Once again, Scotland ran out victors, only this time it was a wee bit more resounding: England were hammered 26-6, having conceded a try after 13 seconds, captain John Spencer fumbling near his line to allow John Frame to nip through and score. The margin of victory – a five-try rout – was Scotland's biggest against England since 1905. The win capped a heady week for Scottish rugby. Scotland had won the Calcutta Cup seven days previously, winning at Twickenham for the first time in 33 years – and dramatically so, Peter Brown converting Chris Rea's last-minute try to edge out the auld enemy by a single point, 16-15. (They were also recipients of the wooden spoon in that 1971 Five Nations, but let's not fudge the point.)

Scotland's previous win at HQ, in 1938, was one of the classic routs. Not that the winning margin – 21-16 – was anything to write home about. But the Scots ran in five tries to England's one – tries were only worth three points in 1938 – and would have recorded a thumping victory had they converted all their scores. As it was, they missed all their conversions, though kicker Wilf Crawford can't be blamed too much: the match was played in mist and high winds, and he did belt over two penalties, one from over 50 yards.

Scotland's man of the match was Wilson Shaw, who set up the first, early try of the match with a kick to the corner, scored himself later in the first half, and sealed the deal with a sashay through a thicket of players late in the game; the Guardian talks of a "lightning" player who "ran clean through the defence and scored amid pandemonium". Shaw was carried off the field "shoulder high in triumph". It was just as well Scotland grabbed the opportunity to celebrate with both hands. Since Shaw's match, they have only subsequently won at Twickers on two occasions: the aforementioned 16-15 win in 1971, and a Roy Laidlaw inspired 22-12 win in 1983 which, while deserved, was a scoreline slightly embellished by seven points added in injury time.

3) Scotland 12–30 England (1980)

England sealed their first grand slam since 1957 here, ending 23 extremely dull years of waiting. Now, the game of the campaign was the rumble against Wales at Twickenham. Paul Ringer was sent off for the visitors after a 14-minute cameo which included two episodes of windmilling fists and a high tackle. A late try by Elgan Rees should have sealed the win for the Welsh – who had won four of the last five Five Nations – but Rees neglected to ground the ball near the posts, and the conversion was missed, all of which allowed England to steal the victory thanks to an injury-time penalty from Dusty Hare. Having already beaten Ireland and France, the triple crown, championship, and grand slam was on. "It is a great feeling, and a strange one, to have played three and won three," said captain Bill Beaumont. (His disbelief was understandable; England had been 8-1 shots to win the championship back in January, fourth in a field of five behind Wales, France and Ireland.)

At Murrayfield, with glory beckoning against a team who had started the campaign as 20-1 outsiders, Clive Woodward stepped up to the plate for England. First he skedaddled down the left wing to set up Mike Slemen for the opening try of the game. Soon enough, he was repeating the trick down the opposite flank, John Carleton the beneficiary. Carleton quickly added another and, by the time 30 minutes were up, England were leading 16-0 and cruising to victory.

After the break, Scotland started flinging the ball around, opting to run everything in the swashbuckling manner. They were rewarded with two tries – one a superlative solo effort by John Rutherford – but England went over the line two more times themselves, Carleton becoming the first player to score a hat-trick of tries since 1924. "I am a bit resentful that some people have labelled us a poor side," said Beaumont after being hoisted around Edinburgh on white-shirted shoulders. "It seems like sour grapes to me. Any team that wins both away matches by scoring heavily" – they had won 17–13 in Paris against a much-fancied French side – "must deserve the sort of rewards we have earned."

4) Scotland 6–9 England (1988)

Nobody would claim the Calcutta Cup as an aesthetic masterpiece – a stumpy little pot, it's the Gareth Chilcott of international sporting trophies – though it does have a beautiful history. Ex-pats in India had briefly formed the Calcutta Football Club in the mid-1870s, only to disband and melt down the remaining silver rupees in the club kitty (£60 worth) to make a cup bearing the club's name, which the Rugby Football Union back at home could use for the big England-Scotland showdown. The three-handled cup – the handles being cobras, and an elephant on the lid – was first contested in 1879, retrospectively awarded to the teams for their earlier wins between 1871 and 1878, and has been an annual fixture, wars aside, ever since.

Sadly, it is now jiggered beyond belief. England like to show it off in the Twickenham museum whenever they win it, but only from behind the glass of a safety case, inside which it revolves slowly like a prize on a 1970s game show. The Blankety Blank chequebook and pen of international sporting trophies HA. The most infamous damage to the trophy was sustained in 1988, when … ah, but first, the game. About which there's happily not much to say: Rob Andrew scored a drop goal, while Gavin Hastings and Jon Webb slotted two penalties apiece, one of Webb's a 50-metre matchwinner. "England may have been the birthplace of rugby but today they effectively killed the game stone dead," cried Scotland coach Derrick Grant after the game, of the victorious side's spoiling tactics.

But as anyone who has ever quaffed real ale through hosiery will attest, rugby is not just about the football. And this dire spectacle was retrospectively transformed into one of the most memorable Calcutta Cup occasions at the after-match banquet. England had turned up late to the dinner, only to find the Scots – who had finished their Five Nations campaign and were busy unwinding – had drained all the free bottles of whisky that had been provided. Predictably enough, the event soon descended into a food and booze fight. In the bedlam, Scotland's John Jeffrey and English police constable Dean Richards filled the cup with champagne, dispatched the contents into Brian Moore's face, and scampered out of the hotel and down the Royal Mile. Richards was wearing a tea cosy as a hat.

After an evening showcasing their passing and kicking skills on the cobbled Edinburgh avenues, the cup – along with the players – were the worse for wear the morning after. "Whoopees with the rupees," punned the Guardian, reporting that blazers from both the Scottish and English unions were investigating the matter. Jeffrey was banned for six months, Richards for a game. An Edinburgh jeweller did his best to knock the battered old trophy back into shape, and the world – like the display case at Twickers – continued to turn. Although if this sort of charming buffoonery were to happen in today's painfully serious climate , you can bet your last melted-down coin that it would suddenly stop.

Both teams went into this match, their final game in the 1990 Five Nations, with a chance to win the grand slam. Only one team was given a hope, though. "Scotland will start as underdogs," reported the Guardian on the morning of the winner-takes-all slam showdown, a first in Five Nations history. "England are the bookmaker's favourites at 3-1 on, at the climax of a season that has followed an ever upward curve. If international rugby was a rational business, then the Scots' creaking performances against the Irish and the Welsh would point to a severe drubbing by England. Thus far, David Sole's team have scored just five tries compared to England's 11, with two of them coming against the 14 men of France. In addition, the Scots have been missing a worrying number of penalties, while the England full-back, Simon Hodgkinson, has kicked 74 points in five games for his country."

If international rugby was a rational business … but when Sole led his men out slowly into the Edinburgh afternoon, a show of measured determination that put hot favourites England into a flat spin, we were offered proof that it was not. In the wake of the passionate tumult whipped up by Sole's strut – and a hearty belt of the Flower of Scotland – the hosts went 6-0 up early on through two Craig Chalmers penalties. Jeremy Guscott waltzed over for a try down the left to pull the score back to 6-4, but England would never draw level. Hodgkinson was unwilling to trust his boot in the high winds, so captain Will Carling was forced to run penalties – decisions the Scots took as arrogance. England's attempts to break through the thin blue line repeatedly came to nothing; Carling, Rory Underwood and Richard Hill were battered by John Jeffrey, Finlay Calder and Scott Hastings.

When Tony Stanger bombed over in the right-hand corner to give the Scots a 13-4 lead early in the second half, the jig was effectively up for the visitors. England, defeated, nevertheless ended the championship with a points difference of plus 64, one short of the Five Nations record. But the Scots had grabbed the prize. "That solemnity was a totally conscious decision," said Sole of his pre-match psych-out. "It stemmed from the belief that we wanted England to know from the outset that a grand slam meant as much to us as it did for them, and we were not for a moment going to flinch or be afraid of the battle. The English were extremely confident; we were extremely hungry."

"I wish you could have heard some of the lip Finlay was giving them at the end of the lineout," added Jeffrey. "You couldn't print it if I told you. Just say it was all addressed to the subject of a sharp deflation of arrogance."

Scotland's 1990 victory might just be the greatest team performance in the history of the Calcutta Cup. There is no questioning what the greatest individual effort is. At the end of the 2003 World Cup final, Jonny Wilkinson famously kicked the drop goal that won the Webb Ellis Trophy for England. One thousand, one hundred and sixty eight injury-ravaged days later, he played his next game for his country. He made sure everyone noticed he was back.

"Imagine Tiger Woods missing 30 major championships in a row then shooting a 63 in his comeback at the Open," wrote Robert Kitson in this paper. "Or Roger Federer strolling into Wimbledon after an injury-strewn three-year sabbatical and not dropping a set in the first week. Wilkinson, if he was not up there already, now belongs in that rarefied stratum."

Wilkinson notched the full set of rugby scores in a 27-point haul: a try, a conversion, a penalty, and a drop goal. It was the third time he'd done it, a world record. Admittedly his try was dodgy in the extreme, and Exhibit A when you're arguing with any fool who claims video evidence in sport does away with controversy – Wilkinson's foot was miles into touch, but was waved through by the video referee anyway – but Scotland were on the end of a four-try battering anyway, Jason Robinson scoring twice, Magnus Lund the other.